How to actually leave a job you have already decided to leave

The practice started because of a resignation letter. Not because of anything dramatic — because a competent operations lead spent five months perfecting the letter and never sent it, while continuing to arrive at a job she had privately finished with.

She was not being indecisive. She was being careful. And the carefulness was the thing keeping her stuck, because there is no amount of editing that turns “I am leaving” into something you feel safe sending.

If that sounds familiar, this post is for you.

Deciding is not the hard part

The decision has usually been made long before the letter exists. You know. You have known for months. What you are actually doing is trying to make the decision feel finished, so that leaving does not feel like a risk.

It is a risk. Some risk is unavoidable here, and no amount of preparation removes it. What preparation does is shrink it to a size you can actually carry, which is a much more achievable goal than certainty.

The three things people get stuck on

The gap. “What do I put on the form for the months between jobs?” This one reassures almost nobody once they hear it. Gaps in senior and mid-career work are normal, employers have seen a decade of them, and a plausible story beats a perfect one. “I took four months to move from teaching into operations and finished the move I had been planning for two years” reads fine. Silence reads worse.

The timing. Almost nobody chooses a good moment. There is no good moment. There are only less bad ones, and the least bad one is usually the moment you are ready, rather than the moment you have saved enough to feel safe. That second moment may never arrive, because feeling safe is exactly what you will arrange to keep needing.

The story. You will be asked why you left. Prepare two sentences, say them plainly, and do not sand them down. “The role changed and I did not grow with it” is a complete answer. So is “I wanted to move into a different field.” You do not owe a fuller explanation to a stranger, and a rehearsed-sounding one is worse than a simple one.

What helps more than any of it

Write the plan you would give a friend. Not the fantasy version — the one with dates, savings, target roles, and the two things that could go wrong. Write it down, keep it somewhere you can find it, and look at it when the doubt arrives at 11pm, because the doubt will arrive at 11pm.

That is genuinely most of it. The resignation letter takes four minutes. The plan is the work, and the plan is also the thing that makes you comfortable telling other people, which in practice is what actually moves the date along.

Where I come in

I do not push people out of jobs. If you are with an employer who is worth staying with, I would rather you stayed. I have sat across from enough people who left a good situation on my advice to know how expensive that can be.

What I do is help you work out whether you are actually dreading the job, or whether you are frightened of the paperwork. Those feel identical and they are completely different problems. A Career Strategy Session is 90 minutes and built exactly for that question.

And if you get to the end of it and decide to stay? That is a real answer too. I have never met anyone who was annoyed to be talked out of a resignation they had already written.